Lithium tri-tert-butoxyaluminohydride → HCID 68147422, compound

HRID 1606296Notes

Reaction equation

HRID 1606296 reaction equation
[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][C:25](=[O:27])[CH3:26])[CH:6]=1)(=[O:3])[CH3:2].[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[C:1]([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C@@H:16]([OH:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24][C:25](=[O:27])[CH3:26])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 68146911HCID 68146911, compound

Product 1

HCID 68147422HCID 68147422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 g. of 1,3-diacetoxy-8α-estra-1,3,5(10)-trien-17-one in 30 ml. of absolute THF is agitated under ice cooling with 2 g. of lithium tri-tert.-butoxyaluminum hydride for 45 minutes under ice cooling. The mixture is then introduced into acetic ice water/NaCl and extracted with ether. The organic phase is washed neutral, dried, and evaporated. The residue (1 g.) is purified by layer chromatography; after recrystallization from hexane/acetone, 380 mg. of 1,3-diacetoxy-8α-estra-1,3,5(10)-trien-17β-ol is produced, m.p. 210°-211° C.

Workup

  1. extractionextracted with ether
  2. washThe organic phase is washed neutral
  3. customdried
  4. customevaporated
  5. customThe residue (1 g.) is purified by layer chromatography
  6. customafter recrystallization from hexane/acetone, 380 mg

Sources & evidence

ORD record
ord-4ff3f153850242f4b9eba36f3f7d3457
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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